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Targeting ligand modified reduction-responsive magnetic nano carrier and preparation method thereof

A technology of magnetic nanocarriers and targeting ligands, which is applied in the direction of pharmaceutical formulations, preparations for in vivo tests, and medical preparations of non-active ingredients. Tumor targeting, simple preparation method, enhanced effect of tumor suppression

Active Publication Date: 2017-05-31
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] At present, there have been many reports on the use of amphiphilic polymers to form micelles to deliver drugs. There are also related cases of constructing magnetic nanocarriers for magnetic targeting or magnetic resonance imaging by doping superparamagnetic nanoparticles into amphiphilic polymers. However, there is no report on reduction-responsive magnetic nanocarriers modified by targeting ligands that combine reduction-responsive properties, magnetic targeting, and ligand-targeting multiple properties.

Method used

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  • Targeting ligand modified reduction-responsive magnetic nano carrier and preparation method thereof
  • Targeting ligand modified reduction-responsive magnetic nano carrier and preparation method thereof
  • Targeting ligand modified reduction-responsive magnetic nano carrier and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] With reference to the document J.Am.Chem.Soc.2004,126,273-279, iron acetylacetonate (0.7063g, 2mmol), 1,2-dodecanediol (2.0234g, 10mmol), oleic acid (l .6948g, 6mmol), oleylamine (1.605g, 6mmol), diphenyl ether (20mL) was stirred under argon flow at 110°C for 1h to remove water and oxygen, and the temperature was raised to 200°C (8°C per minute), React at this temperature for 2 hours, stop nitrogen, heat the temperature to 265°C, reflux for 30 minutes, wait for the reaction solution to cool to room temperature, pour the reaction solution into 40ml ethanol for precipitation, 11000r / min*30min, wash with absolute ethanol After three times, it was dispersed in 25 ml of chloroform for preservation.

[0065] The morphology was observed by transmission electron microscopy (TEM), and the results were as follows: figure 2 , the particle shape is nearly spherical, and the particle size is below 10nm.

[0066] Its magnetic properties were characterized by a vibrating sample mag...

Embodiment 2

[0068] Example 2: Preparation of cetyl alcohol-modified chitosan oligosaccharide (CSO-SS-Hex) bonded with reduction-sensitive bond Linker

[0069] 1) Synthesis of a hydrophobic group bonded with a reduction-sensitive bond Linker:

[0070] 3,3'-dithiodipropionic acid (1.50g, 7.13mmol) and DCC (1.618g, 7.84mmol) were dissolved in 20ml of anhydrous DMF, stirred in an ice bath under argon protection for 30min, cetyl alcohol ( 1.729g, 7.13mmol) and DMAP (87mg, 0.713mmol) were added therein, continued to stir the reaction under ice bath for 1h, then transferred it to room temperature and stirred for 2h, added an equal volume of ethyl acetate to terminate the reaction, filtered to remove Dicyclohexylurea, the filtrate was extracted with ethyl acetate after adding a small amount of water, the ethyl acetate layers were combined, concentrated under reduced pressure, and recrystallized in 20ml of methanol / ethyl acetate=1 / 1 mixed solvent to obtain the product Hex-SS-COOH . That 1 H-NMR s...

Embodiment 3

[0077] Example 3: Preparation of cholesterol-modified chitosan oligosaccharides (CSO-SS-Chol) bonded with reduction-sensitive bond Linker

[0078] 1) Synthesis of a hydrophobic group bonded with a reduction-sensitive bond Linker:

[0079] 3,3'-dithiodipropionic acid (1.50g, 7.13mmol) and DCC (1.618g, 7.84mmol) were dissolved in 20ml of anhydrous THF, stirred in an ice bath under the protection of argon for 30min, and cholesterol (2.756g , 7.13mmol) and DMAP (87mg, 0.713mmol) were added therein, continued to stir the reaction under ice bath for 1h, then transferred it to room temperature and stirred for 12h, filtered to remove dicyclohexylurea, concentrated under reduced pressure, and dissolved in 20ml acetic acid The product Chol-SS-COOH was obtained by recrystallization in a mixed solvent of ethyl ester / n-hexane=1 / 1.

[0080] 2) Synthesis of hydrophobically modified chitosan oligosaccharides:

[0081] After dissolving 1 g of chitosan oligosaccharide with a molecular weight ...

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Abstract

The invention belongs to the technical field of biomedical polymer materials and nano-biotechnology and particularly relates to a targeting ligand modified reduction-responsive magnetic nano carrier and a preparation method thereof; the nano carrier is of typical core-shell structure, using superparamagnetic Fe3O4 nanoparticles to form a core wrapped in a reduction-responsive amphiphilic polymer; the reduction-responsive amphiphilic polymer is formed by linking hydrophobic groups to a hydrophilic polymer through linkers with reduction-sensitive bonds; the amphiphilic polymer forms the shell structure of the nano carrier, and target ligands are attached to the surface of the shell under the action of electrostatic adsorption. The carrier is used for carrying hydrophobic antitumor drugs and carrying out MRI (magnetic resonance imaging). The carrier and the preparation method thereof have the advantages that the carrier is able to target at multiple tumors, antitumor efficiency is improved, and toxic and side effects on normal tissues and organs are lowered; the targeting ligands are adsorbed via electrostatic adsorption, no chemical reaction is required, and time and cost are saved; the carrier may respond quickly to tumor high-GSH (high glutathione) microenvironment, allows a drug to be released quickly in tumor cells, and provides enhanced tumor inhibitory action.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials and nano-biotechnology, and in particular relates to a reduction-responsive magnetic nano-carrier modified by a targeting ligand and a preparation method thereof. Background technique [0002] Malignant tumors have become one of the main killers faced by human beings worldwide, causing about 13% of global mortality every year. According to the World Health Organization (WHO) statistics, around the world, nearly 1 million people are diagnosed with cancer every year, and more than 80 million people died of cancer in the past ten years. Although chemotherapy has achieved good results in anticancer treatment in recent years, it causes severe side effects and brings great pain to patients because it does not have tumor targeting in the treatment process. In addition, many chemotherapeutic drugs have problems such as low solubility, poor stability, low bioavailability, and easy multidrug res...

Claims

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Application Information

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IPC IPC(8): A61K47/36A61K47/02A61K49/08A61K49/12A61K49/18A61P35/00C08B37/08
CPCA61K47/02A61K47/36A61K49/08A61K49/12A61K49/1827C08B37/003
Inventor 冯锋曲玮张仲涛柳文媛刘富垒胡乐坚
Owner CHINA PHARM UNIV
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